Simple synthesis of diastereomerically pure phosphatidylglycerols by phospholipase D-catalyzed transphosphatidylation |
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Authors: | Rina?Sato Email author" target="_blank">Yutaka?ItabashiEmail author Hironori?Fujishima Hidetoshi?Okuyama Arnis?Kuksis |
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Affiliation: | (1) Graduate School of Environmental Earth Science, Hokkaido University, 060-081 Sapporo, Japan;(2) Banting and Best Department of Medical Research, University of Toronto, M5G 1L6 Toronto, Ontario, Canada;(3) Graduate School of Fisheries Sciences, Hokkaido University, 3-1-1 Minato-cho, Hakodate, 041-8611 Hokkaido, Japan |
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Abstract: | A simple method for synthesizing diastereomerically pure phosphatidylglycerols (PtdGro), namely, 1,2-diacyl-sn-glycero-3-phospho-3′-sn-glycerol (R,R configuration) and 1,2-diacyl-sn-glycero-3-phospho-1′-sn-glycerol (R,S configuration) was established. For this purpose, diastereomeric 1,2-O-isopropylidene PtdGro were prepared from 1,2-diacyl-sn-glycero-3-phosphocholine (PtdCho) and enantiomeric 1,2-O-isopropylideneglycerols by transphosphatidylation with phospholipase D (PLD) from Actinomadura sp. This species was selected because of its higher transphosphatidylation activity and lower phosphatidic acid (PtdOH) formation
than PLD from some Streptomyces species tested. The reaction proceeded well, giving almost no hydrolysis of PtdCho to PtdOH in a biphasic system consisting
of diethyl ether and acetate buffer at 30°C. The isopropylidene protective group was removed by heating the diastereomeric
isopropylidene PtdGro at 100°C in trimethyl borate in the presence of boric acid to obtain the desired PtdGro diastereomers.
The purities of the products, which were determined by chiral-phase HPLC, were exclusively dependent on the optical purities
of the original isopropylideneglycerols used. The present method is simple and can be utilized for the synthesis of pure PtdGro
diastereomers having saturated and unsaturated acyl chains. |
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